To synthesize a Ugi adduct from
4-chlorobenzaldehyde, tosylmethyl isocyanide, 5-methylfurfurylamine, and salicylic acid in methanol using Ugi 4CR following Explan005. The target compound was ranked 16 in the DEXP014-V1B file from D-EXP014. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.
Procedure
To a one dram vial, charged with methanol (1mL) 5-methylfurfurylamine, 4-chlorobenzaldehyde, salicylic acid and tosylmethyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for at least 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1 day.
ID/ Lib Rank
Solvent
Aldehyde
Amine
Carboxylic Acid
Isocyanide
Ppt Yes/No
158/16
Methanol
4-chlorobenzaldehyde
5-methylfurfuryl amine
Salicylic Acid
tosylmethyl isocyanide
no
Quantity
1000uL
0.5 mmol, 70.3 mg
0.5mmol, 55.7uL
(density=0.997g/ml)
0.5mmol, 69.06mg
0.5mmol, 96.6 mg
Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)
After the vial set out at room temperature for a day and was sonicated, no Ugi product was formed.
Log
2008-01-17
16:55- Charged a vial with 1 mL of methanol.
17:01- Started to weigh out 4-chlorobenzaldehyde.
17:06- Started to weigh out salicylic acid.
17:10- Started to weigh out tosylmethyl isocyanide.
17:15- Added the 5-methylfurfurylamine to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:17- Added the 4-chlorobenzaldehyde to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:19- Added the salicylic acid to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:22- Added the tosylmethyl isocyanide to the vial and vortexed for one minute. A clear solution was obtained.
17:25- A photo was taken after all of the components were mixed. The solution was left to sit for a day at room temperature.
2008-01-18
17:33- Took picture of the vial. No precipitate has formed yet. The solution was very dark green
17:35- Put the vial into the sonicator for ten minutes.
17:45- Removed the vial from the sonicator. No precipitate has formed.
Objective
To synthesize a Ugi adduct from4-chlorobenzaldehyde, tosylmethyl isocyanide, 5-methylfurfurylamine, and salicylic acid in methanol using Ugi 4CR following Explan005. The target compound was ranked 16 in the DEXP014-V1B file from D-EXP014. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post.
Procedure
To a one dram vial, charged with methanol (1mL) 5-methylfurfurylamine, 4-chlorobenzaldehyde, salicylic acid and tosylmethyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for at least 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1 day.(density=0.997g/ml)
Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)
Results
all components
(158A)
all components
(158B)
Discussion
All results are recorded Master Table and Workflow Tables.
Conclusion
After the vial set out at room temperature for a day and was sonicated, no Ugi product was formed.
Log
2008-01-17
16:55- Charged a vial with 1 mL of methanol.17:01- Started to weigh out 4-chlorobenzaldehyde.
17:06- Started to weigh out salicylic acid.
17:10- Started to weigh out tosylmethyl isocyanide.
17:15- Added the 5-methylfurfurylamine to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:17- Added the 4-chlorobenzaldehyde to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:19- Added the salicylic acid to the vial and vortexed for 15 seconds. A clear solution was obtained.
17:22- Added the tosylmethyl isocyanide to the vial and vortexed for one minute. A clear solution was obtained.
17:25- A photo was taken after all of the components were mixed. The solution was left to sit for a day at room temperature.
2008-01-18
17:33- Took picture of the vial. No precipitate has formed yet. The solution was very dark green
17:35- Put the vial into the sonicator for ten minutes.
17:45- Removed the vial from the sonicator. No precipitate has formed.
Tags
4-chlorobenzaldehyde
tosylmethyl isocyanide InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 InChIKey: CFOAUYCPAUGDFF-UHFFFAOYAC
5-methylfurfurylamine InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3 InChIKey: YSEAGSCGERFGBL-UHFFFAOYAH
salicylic acid InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) InChIKey: YGSDEFSMJLZEOE-UHFFFAOYAQ